Less than three hours from NYC, accessible only by ferry, Shelter Island offers families a fantastic vacation escape that feels worlds away from the city. You won’t find chain stores or even a traffic light on this sleepy island that feels more understated and under-the-radar than the bustling Hamptons. What the island does offer is plenty of fun activities for family bonding. We’ve rounded up the best activities for families on Shelter Island to enjoy with your crew.
One third of Shelter Island is a gorgeous woodsy oasis with 10 miles of coastline. Mashomack Nature Preserve boasts beautiful hiking trails from 1.5 to 11 miles long. The shortest trail is ideal for young families and features reading stations with oversized pages and illustrations from a children’s book spread out along the hike. Mashomack also hosts family-friendly events including outdoor story times, fishing hauls and firefly spotting.
Courtesy of Peconic Watersports
Peconic Watersports will pick up your family on the town dock in Shelter Island Heights for what promises to be an unforgettable outing. Their sleek Malibu wakeboard boats, impeccable gear, and top notch, friendly staff make it easy to dive in to each new experience. Each boat is stocked with wakeboards, water skis, wake surfers, and tubes so families can choose which options to sample. A highlight for your trip.
Kayak & Paddleboard Expeditions
Courtesy of Venture Out Shelter Island
One of the best activities for families on Shelter Island is paddleboarding on Crescent Beach (AKA Sunset Beach). Venture Out is set up right on the beach so you can rent paddleboards on the spot, no reservations required. The company will also deliver kayaks and paddleboards for free to any beach or location on Shelter Island. They also offer group tours and sunset paddles too.
Courtesy of Finley’s Fiction
A gem of a bookstore, located at charming Chequit Hotel, Finley’s Fiction will delight readers of all ages. An avid reader who is a master at pairing people with great reads, owner Finley Shaw has curated an inspired selection of books by new and up-and-coming authors. With the insight of having four children of her own, Shaw has also sourced a fantastic children’s section, along with a mix of games, puzzles, coloring books, notebooks, and stuffed animals.
If your tribe has a sweet tooth that starts early, head to Kyle’s for the island’s most incredible baked goods. Whether your group loves jelly donuts, chocolate croissants, blueberry muffins, coconut macaroons, or cranberry citrus scones, you will want to reserve them ahead of time, they sell out early. In the afternoons and evenings, head to The Tuck Shop, the island hot spot for ice cream for over 30 years.
Courtesy of SALT Waterfront Bar & Grill
Marie Eiffel Market and French bistro boasts one of the most charming and picturesque locations overlooking Dering Harbor. Marie’s gourmet takeout dishes, soups, and sandwiches are not to be missed (the fresh baked baguettes alone are swoonworthy). The back deck overlooking the water or the café tables and chairs set up in front offer postcard worthy views and a perfect spot for a fun family breakfast or lunch.
Maria’s Kitchen in the town center offers a fantastic Mexican menu that kids will love. Maria is also devoted to offering healthy options as well with a wide variety of smoothies, green juices, veggie wraps, and salads. Families can grab lunch or dinner in her casual backyard.
SALT Waterfront Bar & Grill located at Island Boatyard Marina overlooks the marina and offers guests an excellent sushi and seafood menu. An outdoor bar up a short walk from the restaurant set in a former sailboat, features live music seven days a week.
Relaxing Family-Friendly Hotel
Madison Fender Photography
Set on one of the prettiest and off-the-beaten path parts of the island, The Ram’s Head Inn overlooks Coecles Harbor on an idyllic corner of Big Ram Island. A classic country inn with 17 rooms, families will love the farm-to-table restaurant and sweeping lawn. Parents can unwind in Adirondack chairs while their kids enjoy the children’s playground, tennis, and bocce. A small beach with paddleboards and kayaks provide a great launching point for water adventures. Sunday nights are a highlight here with live jazz in the evenings.
Toys and Treats
All within a block of each other Bliss’ Department Store, Jack’s Marine, and Dabney Lee offer an awesome mix of toys, treats, charms, and outdoor and swim gear for kids. At Jack’s, toys are stacked high and owner Camille’s knowledge of toys in unrivaled. Stop by Bliss’ for Legos, puzzles, swimsuits, Shelter Island gear, and boogie boards. Graphic designer Dabney Lee’s colorful store stocks preppy, cheery stationery, charm bracelets, slippers, backpacks and cheery inflatable water toys.
By Sara Bliss